


How To Pick Up Your Best Friend (a guide on pick up lines, pick up trucks and picking your best friend up)

by bb_bubblepopb33



Category: Assassination Classroom
Genre: Bad Flirting, Bad Pick-Up Lines, Cute, Dorks in Love, Fluff, Fluff and Humor, Friends to Lovers, I'm Bad At Tagging, Idiots in Love, M/M, MaeIso, Pick-Up Lines, okano is also there but only for one scene
Language: English
Status: Completed
Published: 2020-08-17
Updated: 2020-08-17
Packaged: 2021-03-05 19:15:20
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,861
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25950460
Author URL: https://archiveofourown.org/users/bb_bubblepopb33/pseuds/bb_bubblepopb33
Summary: Maehara is extremely confident in his courtship skills, having wooed many women before. So when Nakamura challenges him to make his best friend become his boyfriend by the end of the week, the only natural response is: "Who do you think I am? A coward?" before accepting said challenge and planning to not be single anymore. What Maehara didn't consider was that flirting with his best friend would be a lot harder than he thought. Especially since said best friend is someone he's falling for.
Relationships: Isogai Yuuma & Maehara Hiroto, Isogai Yuuma/Maehara Hiroto
Comments: 15
Kudos: 122





	How To Pick Up Your Best Friend (a guide on pick up lines, pick up trucks and picking your best friend up)

"Hey, Isogai, I have to write a paper for my class. It's about the finer things in life. Do you mind if I could interview you?"

Isogai looked up from his screen, where he was typing out an essay, blinking owlishly at Maehara. "Why do you need to write a paper about the finer things in life?"

Maehara faltered. Usually, he would have had another witty pick up line at the tip of his tongue. Yet, whenever he looked at his brilliantly wonderful, talented, smart, gorgeous best friend, he would lose all trains of thought, losing himself in the bright smile that stretched across the ikemen's face.

"I- uhh. You know what? Don't worry about it. Uhh, see ya later!"

And Maehara quickly dashed away, leaving his friend in a brief state of confusion. Maehara rounded the corner, only to almost bump right into Okano.

The athletic girl raised an eyebrow at Maehara. "Seriously? You're rather pathetic, womanizer. You can't even woo someone you've known for more than a decade."

Maehara was quick to protest, "Hey! I'll have you know that it is much more difficult to flirt with someone I've known for longer than someone I barely know."

“Uh huh. Well, good luck, Maehara,” Okano waved a hand as she walks off, leaving Maehara to slump against the wall.

“Yeah, I am kinda pathetic.”

(*~*)

“Baby, you’re so hot you should have your own warnings on the weather channel,” Maehara paired this with a finger gun.

Isogai took out an earphone from his ear, “Sorry, what did you say, Maehara? Something about the weather?”

Maehara stared before facepalming. How did he not see the very obvious buds in Isogai’s ears? “Umm… I said what lovely weather we’re having.”

Isogai let out a small chuckle that did not make Maehara’s heart go doki-doki. “Really, Maehara? That’s what you wanted to say?” He rolled his eyes before continuing, “Yes, the weather is quite nice today. Do you want to go out together after I finish taking notes from this documentary I was assigned for class?”

Maehara’s heart stopped for a second. “Y-Yes!” He desperately hoped he wasn’t blushing.

Isogai beamed, “Great! We can visit our families too! I’m sure my siblings have missed you.”

Oh. That’s what he meant by together. 

“Yeah. That sounds fun.” 

Maehara regretted accepting Nakamura’s challenge.

(*~*)

“Isogai, there’s something wrong with my cell phone. It doesn’t have your number in it.”

Isogai gave Maehara a confused look, “What do you mean it doesn’t have my number? Did you get a new phone without telling me? You’ve had my number since you first got your phone. Also, we’re literally calling right now.”

Maehara knew he shouldn’t have searched up pick up lines on the internet. 

Nakamura exploded with laughter from the other side of the screen. The blonde girl had randomly, without announcement, requested to FaceTime both of them. But not before sending Maehara a private text to “prove he was doing his challenge” giving Maehara barely anytime to search for the better pick up lines and taking the first one which showed up that wasn’t “My love for you is like diarrhea, I just can’t hold it in”. 

So there sat an Isogai with a perplexed expression painted on his face, a Nakamura laughing her ass off and an embarrassed Maehara wishing he was anywhere else but here.

“Sorry, Isogai, that was just the first pick up line on the internet,” Maehara said, praying Isogai wouldn’t look too much into it.

“Oh, okay. Why were you looking at pick up lines? And why did you tell me one?”

Nakamura’s cackling could probably be heard from Mars.

Maehara dug this hole himself. Now he had to lay in it. “You’re cute.” That was not what he meant to say.

The call suddenly ended.

Maehara wasn’t sure how it had ended. He suddenly got a text from Isogai.

 **prince fcking charming <3**  
sorry accidentally dropped my phone mustve disconnected from the call

 **10/10 husbando material ;)**  
nws

  
 **prince fcking charming <3**  
btw when did you change your contact name in my phone

  
 **10/10 husbando material ;)**  
youll never know :p

  
 **prince fcking charming <3**  
://  
you better not have looked through my text history

  
 **10/10 husbando material ;)**  
ooh you dating someone?

  
 **prince fcking charming <3**  
no! 

Maehara hoped not. Otherwise, he would look even more pathetic, attempting to flirt with his best friend.

His phone pinged, and he looked down to see a text from Nakamura.

 **goddamn blonde gremlin**  
its almost the middle of the week   
youve got no game

 **oblivious idiot in love #7**  
stfu

  
 **goddamn blonde gremlin**  
ur pick up lines are pathetic  
i thought you said you were confident in your courtship skills

  
 **oblivious idiot in love #7**  
you want me to give him flowers and bridal carry him?

  
 **goddamn blonde gremlin**  
take pics or it didnt happen

  
 **oblivious idiot in love #7**  
fck off  
i will get him, watch me

  
 **goddamn blonde gremlin**  
if you say so ^~^

(*~*)

“I just wanted to show this rose how incredibly gorgeous you are.”

Maehara held a deep pink rose to a surprised Isogai. He made sure not to get a red rose since the embarrassment that came with it would be too much for him. Especially since the flower literally screamed “I love you” so instead, Maehara got a deep pink rose. The meaning was close enough and was more of an “I admire and appreciate you” which was true.

Isogai flushed, the same shade as the rose in front of him. He gratefully took the rose and smiled, “Thanks, Maehara. What’s with all these flattering things lately, though?”

Maehara short-circuited, “Uhh, because you deserve it!” He offered his own genuine smile, “You’re amazing, Isogai, and I think you should know that.”

He then proceeded to run away as fast he could.

(*~*)

“There are twenty letters in the English alphabet, right?”

Isogai looked at Maehara from where he was writing a report. “What? No? There’s twenty-six. How could you forget that?”

Maehara clapped his hands together, “Oh, right! I forgot. URAQT.”

Isogai blinked in confusion, “That’s still not twenty-six letters.”

Maehara internally gave himself strength as he prepared for the next line. He winked, “Yeah, that’s ‘cause you’re getting the D later.”

The room was silent.

Maehara watched as Isogai thought over what he said.

“You… are… a… cutie…” Isogai immediately exploded in red when he figured out the innuendo behind Maehara’s words.

Maehara flushed as well, feeling the regret of his actions come in way too late.

“I- umm...”

The two guys refused to look at each other.

Maehara knew he shouldn’t have gone for the sex joke. He could’ve just kept it as “there are twenty-one letters in the alphabet” and completely forget about the “D” and everything would have been fine.

“Sorry, was that too forward? It was just another dumb pick up line from the internet. I just wanted to see if it was as stupid as it looked. I didn’t mean it. I’m sorry, this is weird.”

“O-Oh. Uh, yeah. Don’t worry about it.”

The two lapse into an awkward silence as they continue to study, ignoring the thick tension in the room.

(*~*)

“You must be tired because you’ve been running through my mind all day.”

Maehara and Isogai were walking down a quiet, isolated pathway lined with cherry blossom trees, the setting sun seeping through the blossoms, casting soft rays over the pair. 

“I have?” Isogai stopped, turning to face Maehara fully.

Maehara nodded, “Yeah. I’m sorry about that, so let me carry you home.”

Before Isogai could react, Maehara had moved closer, bringing an arm under the ikemen’s legs and swooping him into his arms, bridal style. Without even stumbling, Maehara continued to walk, as if nothing had happened.

Maehara managed to walk a few paces before he felt arms sling around his neck. He felt his head brought down, staring into Isogai’s eyes before his lips met his.

It was a sweet, tender kiss, light as a feather from the wings of an angel, floating down to Earth.

When the two broke apart, broad smiles split across their faces. 

“So, you feel this shirt I’m wearing? This is made of boyfriend material.”

Isogai laughed. 

“Are you sure you didn’t steal it? ‘Cause you seem to be a master of thievery from the way you stole my heart.”

(*~*)

“Hey, Isogai, who needs a pick up line when you have a pick-up truck?”

Maehara sat in the driver’s seat of a polished pick-up truck, smirking at Isogai from the other side of the street. Isogai only shook his head in amusement as he approached him.

“When you said you had our drive taken care of, I didn’t think you’d take the opportunity to make a pun out of it.”

“I only get the best for our first date.”

“Only our first date?”

“Oh, well if you’d like me to bring this beauty to every date?”

Isogai laughed as he made his way around to the passenger seat, “You’re such a dork.”

“Yeah, but I’m your dork.”

“Yeah, you are.”

Maehara took his phone out as Isogai got into the pick-up truck. “By the way, do you mind if I take a picture of us together? I need to send Nakamura proof that I completed her challenge before the end of the week.”

“Nakamura? Wait a second. Was that why she kept texting me you were just practising your courtship skills on me?”

“Wait, what?! She did?!”

“Yeah, but after I told her about your line two days ago, she said she was joking, but you weren’t and that I should seriously consider what you were saying.”

“What did I say- Oh. Uh. Right. Cool. I can’t believe that woman was messing around, though. Trying to sabotage me!”

“Would she really sabotage you if she was the one to bring up the challenge in the first place? I think she was just trying to drag it out long enough so she could brag.”

Maehara moped, making Isogai chuckle.

“C’mon. Let’s take the picture to prove Nakamura wrong, even though she did help.”

 **oblivious idiot in love #7**  
[image attached]  
suck it bish

  
 **goddamn blonde gremlin**  
ur welcome  
i was relenting enough to give up my meddling

  
 **oblivious idiot in love #7**  
if you say so ^~^

Maehara put his phone away after sending the text, looking at his boyfriend.  
  
“So, you ready for the best date of your life?”

Isogai smiled, “Hmm, will I finally get the D?”

Maehara sputtered, almost running his truck into the sidewalk.

(*~*)

“I’d tie your shoelaces so you won’t fall for anyone else but me. Except, you’re not wearing shoelaces, so I guess I’ll have to carry you instead.”

“Are you implying I’d cheat on you?” Isogai teased as he let himself be carried by Maehara across the aisle. 

“Nah, just wanted to carry my newly wedded husband,” Maehara grinned, pressing a quick eskimo kiss at Isogai’s nose. 

“Lemme guess, there’s gonna be a pick-up truck around the corner.”

“You know me too well.”

“I had to write a paper on the finer things in life. It required some pretty thorough research.”

**Author's Note:**

> hoi! ahh this is so bad. this is my first time posting on ao3 so uhh... wow everything is so complicated and im scared i did smt wrong. welp. i hope you like this maeiso oneshot and have a great week. stay safe and uhh, thanks for reading ^o^
> 
> (also planning to do another oneshot called How To Take Out Your Best Friend (a guide on drive-throughs, spy missions and taking out your best friend))


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